


Make Good Decisions

by gardenofmaris



Category: Check Please! (Webcomic)
Genre: (sort of), Accidental Voyeurism, Alternate Universe - Always a Different Sex, Always a girl!Bitty, Always a girl!Jack, Genderbending, Love Confessions, Masturbation, Vibrators
Language: English
Status: Completed
Published: 2016-09-28
Updated: 2016-09-28
Packaged: 2018-08-18 08:37:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,511
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8155909
Author URL: https://archiveofourown.org/users/gardenofmaris/pseuds/gardenofmaris
Summary: Shitty gaped at Bitty in surprise, placing a hand over her mouth. “There's no way. You've got to be kidding me, Bits.”Bitty bit her bottom lip, blush deepening, and shook her head. “I wish I was kidding you, but no. I'm being completely serious.”Shitty finds out that Bitty has never masturbated/had an orgasm before, and ends up creating a chain of events that she could have never predicted.





	

**Author's Note:**

  * For [lilyaugust1](https://archiveofourown.org/users/lilyaugust1/gifts).



> I was talking to the fantastic spockoandjimjim on tumblr, and we got on the subject of fem zimbits and vibrators. Sorry this took so long, darling, but I hope you enjoy <3

Shitty gaped at Bitty in surprise, placing a hand over her mouth. “There's no way. You've got to be kidding me, Bits.”

Bitty bit her bottom lip, blush deepening, and shook her head. “I wish I was kidding you, but no. I'm being completely serious.”

“Brah.” Shitty reached forward to grab Bitty's shoulders and pull her into a hug, petting her hair. “You poor thing. I can't believe you've never had an orgasm. Or even masturbated in general. We _have_ to fix this.”

“Woah woah woah, Shits. Back up a second.” Bitty pulled herself out of Shitty's arms, taking half a step back to better look at her friend's face. “What do you mean?”

“What I mean is,” Shitty started, voice raising, and Bitty suddenly knew that Shitty had a plan no one would be able to talk her out of, “that you shouldn't have to feel ashamed of getting to know your body. There is something absolutely amazing in figuring out what you like, what you don't like, what does and doesn't work for you. The female orgasm is a _beautiful_ thing, and you need to have one like yesterday. Which is why I'm taking you to a sex shop and buying you whatever you want.”

Bitty was sure her face had melted off from how hot it currently felt. “Shitty, you really don't have to do that,” she murmured. “There's nothing wrong with my hands. And besides.” Her voice went softer and she looked down. “I wouldn't even know how to use them properly.”

Shitty gasped, covering her mouth again. “You don't know how sex toys work? What about female reproductive anatomy?”

Biting her lip, Bitty shook her head. “It's not like they were going to teach us anything like that in school. And I may take to the Internet like a hog to mud, but there are some things that are just too embarrassing to search. What if someone saw, you know? I mean, I barely could figure out I'm a lesbian without feeling paranoid every second of the day that someone was going to tell me they knew.” She shrugged. “And I told myself that I'd learn when I came to Samwell, but it still feels a little wrong.”

She was quickly pulled into another hug, and Shitty kissed the top of her head. “Okay, then, First things first. I'm going to teach you the basics. Shitty's Sex Ed 101. Come on.”

~ ~ ~

Hours later, she crawled into bed, mind reeling with all sorts of information.

“Oh my good lord,” she whispered, pulling Señor Bun close and burying her face in the top of his head. “Shitty knows a lot about vaginas.”

She looked over at the sheet of paper on her bedside table that contained all the sites and resources that Shitty told her she could look over when she had free time.

“ _There isn't that much to the basics,”_ Shitty had said, writing another website with a flourish of her hand. _“But there is a lot more out there. There are all sorts of things you can learn.”_ Tilting her head, she'd pursed her lips for a moment as she went over the list one more time. Folding it up, she pressed it into Bitty's hands, closing them around the paper before smiling kindly at her. _“It's all very fascinating actually. You're going to be just fine. And hey, I'm here for you too.”_

Smiling at the memory, she rolled over, closing her eyes and snuggling deeper into the blankets as she drifted off to sleep.

~ ~ ~

A firm, steady knock at Bitty's door woke her up, and she looked blearily at her alarm clock, frowning. Boo. It was already ten o'clock, which meant she wouldn't be able to complain that it was too early to get up.

She closed her eyes and took another deep breath, when the knock sounded again, more insistent. This time, Shitty's voice floated in through the door. “Wake up, sleepyhead. You should get ready.”

Get ready? Bitty stumbled out of bed and yawned as she opened the door, squinting at Shitty while her eyes adjusted to light. “What do you mean?”

She stepped to the side as Shitty walked in and plopped on her rumpled bed. “I mean, that now that you know what to do with a sex toy, we're going out and I'm going to buy you one.”

Bitty blinked rapidly at Shitty, tilting her head to the side. “But won't my fingers work too? That's what you said last night.”

Shitty smiled fondly at her. “Of course they do. Your fingers can do some magical shit, brah. But sex toys are pretty amazing too, especially when they're free. And I'm gonna pay for it, so it's pretty much free for you.”

Having been rummaging through her closet for clothes, Bitty popped her head out in shock. “You really don't have to do that,” she protested, face red.

“Don't worry, brah, I've totally got it.”

~ ~ ~

“Seriously, you don't have to do this for me.” Bitty gawked at the price tag on one of the smaller vibrators. Forty dollars? That was fine for baking supplies, but she didn't even know how often she'd use the vibrator.

Shitty smiled and shook her head, making a 'don't worry about it' gesture. “It's totally fine. It's not like I'm exactly broke or anything. Get whatever you want and don't worry about the price.”

“Okay.” Bitty's tone was dubious, but she knew better than to question Shitty. “So what's the difference between all of these? They all look the same to me honestly.”

“Yeah, that makes sense.” Shitty nodded sagely. “There are definitely a lot of similarities. Once you know what you're looking for, though, it's easier. For example, the Haus has paper thin walls and you don't live alone when you go home, so something silent will work best. You can also decide whether or not you want it to be waterproof. I don't really care, since I don't use mine in the shower, but you might want to do that. You can also decide on how big you want it to be. Some,” she continued, picking a seemingly random package off of the wall and showing it to Bitty, “are tiny and discreet, like this one. It's disguised as a lipstick tube. That way anyone snooping around will think it's just makeup or something.”

“Woah.” Bitty stared down at the package with wide eyes, flipping over the package and looking over the different specifications of the vibrator.

“Yeah,” she laughed. “It's pretty great.”

They wandered around, checking out different vibrators (Bitty just shook her head and scrunched her nose up when she saw the dildos), Shitty doing a running commentary and answering all of Bitty's questions. They finally found one they thought would work nicely and Shitty tilted her head in the direction of one of the workers there, saying they should go ask about it. Bitty panicked for a moment, realizing that the person would take one look at her and know what she was going to use it for. Shitty picked up on it pretty quickly though, and placed a comforting hand on Bitty's shoulder.

“It's their job,” she reassured. “I bet you they really don't care, and they often have really good advice about how to use a particular one or whether or not it's even worth the money. Plus, they have batteries on hand to make sure the toy works and the vibrations are to the strength of your liking.”

Bitty bit her lip, looking down and shifting from foot to foot. “It's just kind of embarrassing.”

Shitty's face softened and she nodded. “If you want, I can do most of the talking. You can just double check and make sure that you like it and understand how it works.”

She thought it over for a second before nodding, smiling gratefully up at Shitty. “I'd really like that, thank you.”

Her answering grin was priceless. “Perfect. Come on.”

~ ~ ~

Bitty walked out of the shop with Shitty, feeling excited about her new possession. She wrapped the bag around everything and stuffed it into her purse, a bounce in her step as they walked back to the Haus.

It felt like an eternity and a moment simultaneously, and Shitty gave her a knowing look and made a 'shoo'ing motion. “Go on, girl. Get your first orgasm. I hope it's a great one. I'm just gonna grab a book out of my room, and since everyone is off doing their own things, I'm gonna head to the library, and you'll have the Haus to yourself.”

Bitty blushed brightly but nodded, and they each headed to their respective rooms.

She waited until she heard the front door close and pulled out her phone, pulling up a good playlist that she played whenever she needed a good confidence boost. It definitely would help with the psychological aspect of orgasm, or at least that's what Shitty had told her the night before, and it would also mask any vibration noise (she hoped).

Double checking that the door was firmly locked, she sat down on her bed and pulled the bag out of her purse. The package was simple to open, and she pulled out the batteries as well, putting them in the way the worker had shown her to. She fiddled with the button, feeling it buzz to life in her hands. Cycling through the three different intensities and multiple patterns of vibrations, Bitty imagined what it might feel like when she finally put it to her vagina. She pulled out the toy cleaning spray the worker had also recommended and cleaned it, wiping her hands off on her shirt when she was done.

Taking a deep breath, she moved through the cycles until it turned off, before laying back down on the bed. Figuring it might make the whole experience a little bit easier if she explored everything with her fingers first, she unbuttoned her jeans and reached her hand in under the waistband of her panties.

Her fingers curled in the short coarse hairs that covered her skin there. It was a new feeling, a lot like when she combed her hair with her fingers, but different simply because of the texture. She bit her lip as her fingers went further down. Sure, her hand had been close to her vagina before, but it was almost strange thinking that now it was for a different purpose. It seemed almost anticlimactic when her fingertips brushed against her labia and it simply felt like more skin. It filled her with courage to know that this was okay, that this was good even, and she eagerly parted the lips of her labia, rubbing her fingers along the much smoother skin protected by them.

She familiarized herself by touch for a little longer, until the angle of her hand and the pressure of her waistbands made her wrist start to cramp up. When that happened, she pulled her hand out and wiped it off on her pant leg before looking over at the vibe laying innocuously on the bed next to her. Her heart sped up at the thought of her first orgasm, and she practically threw off her pants and underwear.

Immediately, she felt a little shy, being half naked out in the open, even if she was alone in her room. She had the urge to hide under her comforter, but she also wasn't entirely certain that she would be able to do everything right if she couldn't see what she was doing.

Turning the vibrator on its lowest setting, she pressed it up against her labia, humming softly at the new and slightly pleasant feeling. It wasn't much though, so she moved it around until it finally came to rest on her clit. A warm feeling bloomed in her lower belly, extending even to her toes.

Eventually, she started moving it around on her clit, and she couldn't help the tiny moan as the friction increased that nice warm feeling. The more she did it, the braver she felt, and the more she wanted, so she pressed the button for the next setting. The vibrations intensified, and her toes curled. Her body felt a few degrees hotter, and the knowledge that she was alone made her unashamed when she couldn't help but moan. On some level, it felt narcissistic that the sound of her own moan turned her on a little more, but she didn't really care.

She pulled the vibrator off her clit for a second and let her hand wander back down to feel how her arousal had changed it. It was a little shocking when she felt her own wetness touch her fingers, and she couldn't help but run her fingers through it. Her fingers slid up wetly to her now swollen clit, and she marveled and how much bigger and smoother it had felt than when she wasn't aroused. Curious, she rubbed with her slick fingers and it created a feeling just like her vibrator, if a little less intense. God, this was so amazing. She couldn't believe she'd never done this before.

Deciding to leave the highest setting for a later time, Bitty reached for the vibrator again, already practically addicted to the feeling. She couldn't help the soft moans and gasps as her hips bucked and rolled, seemingly of their own volition. Her body was taking the sensations greedily, and it made her dizzy with how good it felt.

She could feel the sensation in her stomach building higher and higher, and her toes curled up as tight as possible. Her hips rose, and she found herself imagining warm, strong hands holding onto her hips. Bitty could practically see the gorgeous blue eyes watching her hungrily, and she gasped out a broken word when the spring in her abdomen finally snapped and a full body shudder ran through her.

With just barely enough presence of mind, she turned off the vibrator and dropped it onto the sheets, chest heaving as she caught her breath. Her entire body felt shaky and sated, and she could feel a heaviness in her eyes that betrayed her sudden burst of sleepiness. She smiled and pulled off her shirt, before curling up under her comforter and falling asleep.

~ ~ ~

It took no time at all for Bitty to fit masturbation into her schedule. After all, she felt so much happier and so much less stressed nowadays. Sure, baking was her number one way to relieve stress, but on the days when even the push and pull of her muscles as she rolled out dough failed, a good orgasm helped a little at least.

There were only two downsides to it, she found. One, she wasn't very quiet. She'd tried, but with everything being so new, it was almost impossible to hold back the little moans and whimpers that wanted to escape her throat. Granted, she didn't try as hard as she could have, just because it turned her on to hear it. But regardless of why, the fact was that she couldn't keep quiet, which meant that she had to wait until everyone was gone before she was able to get off. It could get frustrating at times, but luckily for her, she already knew everyone's schedules. She wasn't ashamed to admit it, but she knew when her opportunities would arise, and she took them more often than not.

The second downside, and honestly it probably shouldn't have surprised her as much as it did, was that almost every single time, her thoughts would turn towards Jack. She'd had a crush on her captain since a little while after they'd become friends, and as her feelings got stronger, Jack started showing up in her fantasies more and more often. Not that it was the first time, to be completely honest.

Before Shitty had opened her mind to the beauty that was masturbation, she'd already been having fantasies about Jack. She fantasized about Jack coming home after a long day and leaning down to kiss her sweetly, about Jack smiling at her unguarded, eyes shining with her happiness, about curling up on the couch with Jack to watch a movie or whatever documentary caught Jack's eye. That wasn't to say that she didn't dream of that anymore, but now there were more scenarios. Jack picking her up and setting her on the counter to eat Bitty out, Jack propping her naked body above Bitty's, driving Bitty insane with her touches and kisses, how Jack's face would look as Bitty took time to pleasure her and pull orgasms out of her. Bitty wondered if Jack masturbated too, if she had a vibrator.

It was always fantastic to think about when Bitty was close to orgasm. Most of the time, it gave her that final push that she needed to become a trembling, tired mess. The downside, however, was that it made looking Jack in the eye very difficult. Were it not for the fact that being in the closet made her so good at deflecting the truth, she probably would have cracked within the first week.

Of course, she wasn't really thinking about that when she hit send on her text to Jack (probably because she was drunk out of her mind). She looked at the little question from Jack ('where are you?'), eyes flitting down to her response ('in my room come on up'), and bit her lip as the vibrator hit a particularly sweet spot on her clit.

She was so sick of sitting by and not doing anything. She wanted Jack, and she felt as if Jack wanted her back. So she was offering herself. There was no point in spending her days pining. (Her intoxicated mind easily pushed aside all rational thought in favor of all those fantasies that had been running around her head in the months since Shitty had taught her about masturbation.)

When the doorknob finally jiggled and the door opened, Bitty couldn't help the soft moan at seeing beautiful, wonderful Jack. Her back was turned to Bitty, and she didn't hear the moan over the loud music blasting from the living room where a party was currently taking place. The sounds became muffled once more, however, when Jack closed the door and finally turned so that she could look at Bitty, a sentence starting to come out of her mouth.

The sentence died quickly however, the words lingering in the air between them as she finally took in the scene in Bitty's bedroom: Bitty, completely naked, legs spread as her hand moved her vibrator between her legs. Jack's eyes widened, and her mouth dropped open as she stared openly.

Bitty would be lying if she said that she wasn't nervous at all, but not only was she drunk as hell, the sensations currently bombarding her were fantastic and she didn't want them to stop. “Jack,” Bitty whimpered, reaching out with her free hand and beckoning her closer.

She was expecting Jack to come stumbling towards her and join her in bed. She wasn't expecting Jack to back up quickly and run out of the room, door slamming behind her.

~ ~ ~

The light coming in from Bitty's brand new curtains brought in a horrible, almost blinding headache, and her eyes were completely closed. She pulled her pillow over her head and groaned, frowning deeply when the noise aggravated her headache.

She was halfway back to sleep when she remembered what she had done the night before. Her eyes shot open, and even through the pain in her head, she frantically reached for her phone.

“Please don't be real. Please don't be real,” she whispered, pulling up her phone's text conversation with Jack, only to let her head drop when she saw that yes, it was very real. “Fuck,” she gasped, chest tight. She never meant to do any of that.

Her heart dropped even more when she saw the newest message in their conversation, a simple, short 'We need to talk' from Jack, received only about an hour before. She swallowed hard as she sent back 'What time and where?'

The response was so fast, Bitty knew Jack was going to be serious. The only thing she'd ever responded this fast for was checking practice.

She could swear that two seconds and a million years passed simultaneously before she had to go meet Jack at their agreed location. As she walked to Annie's, her skin felt just a little too tight and she was shivering lightly as if she was cold, even though she was actually quite warm for once.

A million different thoughts ran through her head. What if she was kicked off of the team? What if Jack was digusted by her? But the thought that hurt her the most was the faintest idea that Jack might stop being her friend, start being mean to her all over again. Her shivering intensified at that thought and she whimpered under her breath, hoping and praying that wasn't what was going to happen, although with how stupid she'd been, that was probably what was going to happen. She almost broke down right there in the middle of the street, but was able to pull herself together at the last moment. If she was going to lose Jack, she sure as hell wasn't going to cry in public.

Setting her jaw when she saw the all too familiar sign, Bitty took a deep breath and pushed open the door. The little 'ding' that announced her presence made her wince, but she walked in regardless and looked around, before spotting Jack in the back corner of the shop.

She took a deep breath and steeled herself for whatever was going to happen, before slipping into the seat across from her captain. “Hi,” she whispered.

Jack's head lifted, and Bitty's heart almost stopped at the sight of Jack's gorgeous blue eyes staring at her. It was both ridiculously attractive and terrifying. Then again, she mused, there was a reason this woman pretty much brought her to her knees.

“I'm going to be very blunt right now,” Jack started, and Bitty's heart clenched up even more. “What you did was unacceptable.”

Bitty flushed deeply and nodded, looking down and trying her best not to cry. She swallowed, but her voice was still thick when she started speaking. “It was. I crossed a line last night, and I'm so sorry. I did it because I was drunk, but that's still no excuse.”

Jack's hand reached over to gently touch Bitty's shoulder, and she couldn't take it anymore. She sobbed lightly, wiping away her tears quickly, muttering apologies.

“What are you sorry for?” Jack's voice sounded almost confused, but that couldn't be right. She was upset with Bitty right now.

“I'm sorry for everything. For crying, for making a scene, for pushing myself onto you when you're obviously straight.” Her voice broke a couple times, and she tilted her entire self away from Jack to give herself some room to compose herself.

“Oh shit,” Jack muttered, before standing up and reaching her hand out towards Bitty. “We should probably go somewhere more private.”

Bitty nodded and followed Jack, her head tilted down so no one could see that she'd been crying. They ended up in a little public park, but it wasn't as popular as the other one a block away so almost no one was there. The two or three joggers there were absorbed in their music and paid them no attention.

Jack sat Bitty down on a picnic bench and sat down next to her, gently wiping away what was left of Bitty's tears. “Come on, Bitty,” she murmured. “Talk to me. Why do you think that what you did was unacceptable?”

Bitty bit her bottom lip, but refused to hold onto the things that were eating her up. “You're straight. I know that. Everyone else knows that. And I disregarded that respect and threw myself at you in a really vulgar way, just because you looked at me nice a few times and I thought that maybe you liked me back.” She cleared her throat, wrapping her arms around herself.

She could hear a shocked intake of breath from Jack and looked up, head tilting at then different emotions flickering across her face like a strobe light. “What?” Bitty asked, voice small. She was honestly starting to get confused.

“You were propositioning me?” Jack's voice sounded strangled, and Bitty's confusion rose into a tidal wave.

Bitty looked at Jack like she'd grown another head. “You're kidding right? What else did you think I was doing?”

Jack looked to the side, eyes wide and shock written all over her features. “I thought you just answered my text because you weren't thinking about what you were doing and how I would see you. I thought you were just drunk and horny. I thought a bunch of different things, but I didn't think that you actually _wanted_ me to be there.”

Bitty burst into hysterical laughter. “Are you joking right now? Because I seriously have no idea how much more clear I could have been.”

Jack also laughed softly, a hint of confusion and hysteria audible, before turning back to Bitty. “So you really like me? You want me?”

“How could I not?” Bitty took a deep breath, scared of what would happen when she said more, but knowing that she couldn't stay quiet anymore. “It's not just that you're gorgeous, even though you really really are. It's that you're sweet, and caring, and passionate, and you're the dad joke extraordinaire. It's that you've gone through hell but you still came back and learned how to love and be loved. You're fantastic, and I don't know how anyone could know you without falling absolutely in love.”

Bitty shut her mouth with a 'click' when the word 'love' left her lips. “So yeah,” she mumbled.

Jack stared at her for a few moments, blinking multiple times and opening her mouth at least three or four times only to shut it, before she visibly shook herself and turned to face Bitty. “Can I kiss you?”

Bitty would deny until the end of time that she squeaked when those words left Jack's lips. “What?” she gasped.

Jack's responding smile was smitten in a way Bitty had never seen it before. “Can I kiss you?”

She couldn't respond verbally, so overcome with shock and emotion, so instead she nodded.

Feeling Jack's lips on hers was a brand new religious experience. It was so much better than she'd imagined. Jack's mouth, lips, tongue, hands, fingers, her very presence was intoxicating. Sure, Bitty figured she could learn more, but as far as first kisses went, this one felt fantastic.

She laughed softly when Jack pulled away, leaning forward to rest her forehead on her shoulder. “So you're not straight?”

Feeling Jack's body move up and down as she laughed was something Bitty didn't think she'd ever get over.

“You tell me.”


End file.
